| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1314004 | Journal of Fluorine Chemistry | 2013 | 4 Pages |
Treatment of ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate (3) with TBAF in the presence of MS4Å followed by addition of an aromatic aldehyde afforded ethyl (E)-4,4-difluoro-5-hydroxy-5-arylpent-2-enoate (1) that was a versatile intermediate for constructing a stable isostere of peptide or fluorinated sugar molecules. This strategy offers straightforward approach to synthesize such a versatile intermediate (1).
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Ethyl 4,4-difluoro-3-(triethylsilyl)but-3-enoate (3) was synthesized. ► 3 generates 4,4-difluorocarbanion by treatment of 3 with TBAF. ► The generated 4,4-difluorocarbanion attacks to aldehydes. ► 3 serves good building block for constructing β,β-difluorohomoallylic alcohols.
